You know that moment when being the “nice one” stops feeling kind and starts feeling crushing? That’s where our final caller of the season finds herself: kind, empathetic, beloved by her coworkers—and drowning under the weight of everyone else’s problems. She’s not a manager. She’s not an HR rep. But somewhere along the way, she became the unofficial office therapist. And now, the constant venting, after-hours texts, and emotional labor are burning her out.

In this season finale, Jenny responds with her signature mix of warmth, wit, and straight-up wisdom. She holds space for what it means to be “the one everyone turns to”—especially when it starts to cost you your own peace. Jenny doesn’t just validate the exhaustion; she offers a powerful strategy: bore them. Yep. Get boring. Cut off the energetic supply with compassion, consistency, and just the right amount of weather talk. It’s about training the office to see you as capable—but not constantly available. Supportive—but not their sponge.

This episode isn’t just about workplace boundaries—it’s about reclaiming your energy in a world that too often rewards emotional over-functioning. Jenny reminds us that empathy is a gift, but it’s not a job description. Whether you’re navigating your own “office therapist” moment or learning to reset long-standing dynamics, this finale will leave you seen, supported, and ready to say: I love you, but no.

In this episode of Jenny Says So, Jenny dives into the complexities of friendships—specifically how to navigate awkward moments and misunderstandings with grace and empathy. She emphasizes the importance of curiosity and open communication, suggesting that friends should approach conflicts with a mindset of understanding rather than judgment. Jenny shares her tips for creating safe spaces for vulnerability, addressing misunderstandings directly, and handling tense moments with compassion and clarity.

Jenny dives into this relatable friendship dilemma with her signature compassion and straightforward advice. She discusses how easy it is to misread tone through text and emphasizes the importance of face-to-face communication to clear up misunderstandings.

Jenny shares practical tips on how to address inconsiderate behavior with kindness and honesty, suggesting that open-ended questions can help uncover intentions without placing blame. Her advice highlights the importance of curiosity, understanding, and direct communication in navigating friendships.

In this episode of Jenny Says So, Jenny dives into the complexities of social obligations when friends or acquaintances visit a city. She emphasizes the importance of setting boundaries, being authentic in interactions, and managing expectations. Jenny also shares practical advice on how to prepare for visitors, including creating a recommendations list and practicing responses to maintain personal well-being.

Jenny dives deep into this relatable situation, offering heartfelt advice on setting boundaries, honoring your own time, and not feeling obligated to play tour guide when it’s not genuinely aligned with your energy. She shares tips for gracefully saying no, offering curated recommendations instead of your time, and recognizing when a visit is more about convenience than connection.

Jenny encourages listeners to listen to their instincts, practice direct communication, and prioritize their own well-being without guilt. Her practical advice is perfect for anyone feeling the weight of social obligations and looking for a way to protect their time while still maintaining meaningful connections.

In this heartfelt episode, Jenny dives into the emotional complexities of setting boundaries—especially in adult relationships with parents. Prompted by a listener question about navigating caregiving concerns while protecting one’s emotional wellbeing, Jenny shares her perspective on how to honor both compassion and self-respect. She explains the difference between communicated boundaries (what we say) and internal boundaries (what we do or don't allow ourselves to absorb), reminding listeners that healthy relationships require both.

Jenny gently affirms that we are not responsible for managing the lives or emotions of capable adults—even our parents. Holding back unsolicited advice, saying no without guilt, and recognizing when certain conversations may do more harm than good are all essential tools in maintaining emotional balance. She speaks candidly about the grief that can come with realizing some family members may never change—and how that realization can actually open the door to peace, clarity, and deeper healing.

Therapy, Jenny emphasizes, can be a powerful companion on this journey. Finding a therapist who truly “gets you” can help unravel generational patterns and empower you to make loving yet firm decisions. Ultimately, Jenny reminds us that prioritizing our mental health isn't selfish—it’s necessary. This episode is a reassuring listen for anyone learning how to balance love, boundaries, and the difficult truths of family dynamics.

Learn more about Jenny Says So Podcast: https://www.freshstartsregistry.com/jenny-says-so-podcast

In this episode of Jenny Says So, Jenny tackles the tricky topic of wedding gift expectations and whether guests should feel obligated to give one—especially when attending a wedding already comes with significant costs. Responding to a heartfelt listener question from Guilt-Stricken Wedding Guest in Wisconsin, Jenny breaks down the financial realities of being a wedding guest, the social pressures around gift-giving, and why celebrating love shouldn’t come with a price tag. She challenges the idea of quid pro quo in weddings, emphasizing that gifts should come from a place of joy, not obligation.

From navigating tight budgets to finding thoughtful, affordable ways to show your support, Jenny shares practical advice for guests who may feel guilty about not giving a traditional gift. She also highlights the importance of self-care, setting financial boundaries, and shifting the focus back to what truly matters—celebrating the couple’s love. Whether you’re planning a wedding, attending one soon, or simply rethinking the way we approach gifting, this episode offers a refreshing, judgment-free take on modern wedding etiquette.

Learn more about Jenny Says So Podcast: https://www.freshstartsregistry.com/jenny-says-so-podcast

This week on Jenny Says So, Jenny tackles a question from a listener, Stuck on Small Talk in South Carolina, who wants to move beyond surface-level conversations but isn’t sure how. They find themselves lost when sports and weather come up, wondering how to transition to more meaningful discussions.

Jenny breaks down the art of small talk, explaining that no conversation is truly small when approached with curiosity, openness, and intention. She offers practical tips for engaging in deeper conversations, including asking thoughtful questions, sharing personal stories, and embracing moments of vulnerability.

Jenny emphasizes that every interaction is an opportunity to build connection and that light conversations can often lead to heartfelt moments if we’re willing to step outside our comfort zones. She shares strategies for making conversations more engaging, fostering authenticity, and creating space for deeper dialogue. Whether you're looking to improve social skills, build stronger relationships, or simply feel more confident in everyday interactions, this episode will give you the tools to transform small talk into something truly meaningful.

Learn more about Jenny Says So Podcast: https://www.freshstartsregistry.com/jenny-says-so-podcast

This week on Jenny Says So, Jenny tackles a question from a listener, Guilt About Gifts in Georgia, who’s unsure about the etiquette of bringing gifts when visiting someone’s home. From housewarming parties to casual get-togethers, they wonder when a gift is expected—or if it’s even necessary.

Jenny breaks down the nuances of guest gifts, reassuring listeners that while a small token of appreciation is always thoughtful, showing up empty-handed is perfectly fine, especially if the host insists. The key is understanding context, relationships, and cultural expectations rather than following rigid rules.

Jenny shares practical insights on navigating gift-giving with confidence, emphasizing that a simple gesture—like bringing dessert, a bottle of wine, or even just asking if the host needs anything—can go a long way. She also explores how different cultures view guest gifts, the role of re-gifting, and why assuming the best intentions in social interactions helps create a more welcoming environment. If you’ve ever stressed about whether to bring a gift, this episode will help you approach it with ease and authenticity.

Learn more about Jenny Says So: https://www.freshstartsregistry.com/jenny-says-so-podcast

In this heartfelt episode of Jenny Says So, Jenny tackles a listener’s question about how to support a close friend who lost everything in a devastating wildfire.

From afar, it can be difficult to know what to say or do, but Jenny introduces the VASE method—Validate, Acknowledge, Support, and Express—as a thoughtful approach to providing comfort and care. She offers compassionate advice on validating the enormity of your loved one’s loss, acknowledging their pain, and offering practical and emotional support without overstepping boundaries.

Listeners will come away with actionable tips for helping friends in crisis, such as offering financial assistance, coordinating logistical help, or simply reaching out with heartfelt words of love and connection. Jenny emphasizes that even small gestures can have a profound impact during times of overwhelming grief. Whether you’re near or far, this episode will inspire you to show up with kindness and care for the people who matter most.

To support people who have lost their homes in the wildfire, please check out this link!

To create a free registry to help people start over again, check out the registry and essential items bundles here: https://www.freshstartsregistry.com/registry

In this episode of Jenny Says So, modern-day etiquette expert Jenny tackles a relatable question from "Don't Want to Feel Weird in Wyoming" about navigating greetings and introductions in mixed social and professional settings. Should you go for a handshake, a hug, or something else entirely? Jenny breaks down how to read the room, establish comfort for everyone, and avoid awkward moments with a thoughtful approach to personal boundaries and cultural norms.

We'd love to know what you think about this episode! Have a question for Jenny? Head to the link and let us know. All questions are totally anonymous.

https://www.freshstartsregistry.com/jenny-says-so-podcast

Thank you to Aunt Jane for providing the voice over work, and the theme song is provided by simonarmitage, Pond5.

In this episode of Jenny Says So, modern-day etiquette expert Jenny tackles a heartfelt question from "No Longer a Hugger in New York." Jenny explores how to navigate shifting personal boundaries, particularly when it comes to physical greetings like hugs. She shares practical advice on communicating changes with warmth and honesty, while also addressing the reactions of friends who might struggle to adapt. With empathy and curiosity, Jenny guides listeners on how to maintain meaningful relationships while honoring their own comfort and autonomy.

We'd love to know what you think about this episode! Have a question for Jenny? Head to the link and let us know. All questions are totally anonymous.

https://www.freshstartsregistry.com/jenny-says-so-podcast

Thank you to Taylor for providing the voice over work, and the theme song is provided by simonarmitage, Pond5.